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Chemical compound From Wikipedia, the free encyclopedia
2-Oxazolidone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring.
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Names | |||
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Preferred IUPAC name
1,3-Oxazolidin-2-one | |||
Other names
2-Oxazolidone 2-Oxazolidinone | |||
Identifiers | |||
3D model (JSmol) |
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ChemSpider | |||
ECHA InfoCard | 100.007.129 | ||
KEGG | |||
PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C3H5NO2 | |||
Molar mass | 87.077 g/mol | ||
Appearance | Solid | ||
Melting point | 86 to 89 °C (187 to 192 °F; 359 to 362 K) | ||
Boiling point | 220 °C (428 °F; 493 K) at 48 torr | ||
Related compounds | |||
Related compounds |
Oxazolidine | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oxazolidinones are a class of compounds containing 2-oxazolidone in the structure. In chemistry, they are useful as Evans auxiliaries, which are used for chiral synthesis. Usually, the acid chloride substrate reacts with the oxazolidinone to form an imide. Substituents at the 4 and 5 position of the oxazolidinone direct any aldol reaction to the alpha position of the carbonyl of the substrate.[citation needed]
Oxazolidinones are mainly used as antimicrobials. The antibacterial effect of oxazolidinones is by working as protein synthesis inhibitors, targeting an early step involving the binding of N-formylmethionyl-tRNA to the ribosome.[1] (See Linezolid#Pharmacodynamics)
Some of the most important oxazolidinones are antibiotics.[2]
Examples of antibiotic oxazolidinones include:
The first ever used oxazolidinone was cycloserine (4-amino-1,2-oxazolidin-3-one), a second line drug against tuberculosis since 1956.[10]
Developed during the nineties when several bacterial strains were becoming resistant against such antibiotics as vancomycin. Linezolid (Zyvox) is the first approved agent in the class (FDA approval April 2000).
The first commercially available 1,3-oxazolidinone antibiotic was linezolid, discovered and developed by Pharmacia & Upjohn.[citation needed]
In 2002 AstraZeneca began investigating posizolid, which is in clinical trials for use in humans.[11]
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